One-pot synthesis of 5,5 '-dibromo-2,2 '-dipyridylacetylene and its boronic acid derivative

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5,5'-Dibromo-2,2'-dipyridylacetylene was prepared from 2,5-dibromopyridine and (trimethylsilyl)acetylene via the new one-pot synthesis approach using a regioselective palladium-catalyzed coupling reaction with a 60% yield. Several protocols of lithium-halogen exchange were then attempted to synthesize 6,6'-(1,2-ethynediyl)bis[3-Pyridylboronic acid] from 5,5'-dibromo-2,2'-dipyridylacetylene. The former was successfully obtained with a 54% yield by a reverse addition method using toluene and THF and it showed potential as a useful building block for cross-coupling reactions in the formation of carbon-carbon bonds. (C) 2010 Elsevier Ltd. All rights reserved.
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Issue Date
2010-12
Language
English
Article Type
Article
Keywords

CROSS-COUPLING REACTIONS; HALOPYRIDINYLBORONIC ACIDS; PYRIDYLBORONIC ACIDS; HETEROARYL HALIDES; ARYLBORONIC ACIDS; PROTOCOL; DIARYLACETYLENES; ACETYLENES; LITHIATION; CATALYSTS

Citation

TETRAHEDRON LETTERS, v.51, no.48, pp.6243 - 6245

ISSN
0040-4039
DOI
10.1016/j.tetlet.2010.09.062
URI
http://hdl.handle.net/10203/93551
Appears in Collection
EEW-Journal Papers(저널논문)
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